An approach to the narciclasine alkaloids via a quinone methide initiated cyclization reaction

被引:24
|
作者
Angle, SR
Wada, T
机构
[1] Department of Chemistry, University of California-Riverside, Riverside
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(97)10138-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective synthesis of a possible intermediate for the synthesis of the narciclasine alkaloids from D-glucose is described. The key step of the sequence is a quinone methide initiated cyclization reaction, (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7955 / 7958
页数:4
相关论文
共 50 条
  • [21] Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide
    Adlington, RM
    Baldwin, JE
    Mayweg, AVW
    Pritchard, GJ
    ORGANIC LETTERS, 2002, 4 (17) : 3009 - 3011
  • [22] Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide
    Bishop, Lee M.
    Winkler, Michael
    Houk, Kendall N.
    Bergman, Robert G.
    Trauner, Dirk
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (18) : 5405 - 5408
  • [23] Bioactivation of tamoxifen to metabolite E quinone methide: Reaction with glutathione and DNA
    Fan, PW
    Bolton, JL
    DRUG METABOLISM AND DISPOSITION, 2001, 29 (06) : 891 - 896
  • [24] Norbornyl Route to Polyoxygenated Cyclohexanes. An Approach to Pancratistatin and Narciclasine Alkaloids
    Mehta, G.
    Mohal, N.
    Tetrahedron Letters, 39 (20):
  • [25] Norbornyl route to polyoxygenated cyclohexanes. An approach to pancratistatin and narciclasine alkaloids
    Mehta, G
    Mohal, N
    TETRAHEDRON LETTERS, 1998, 39 (20) : 3281 - 3284
  • [26] Syntheses of Chromenes and Chromanes via o-Quinone Methide Intermediates
    Ferreira, Sabrina B.
    da Silva, Fernando de C.
    Pinto, Angelo C.
    Gonzaga, Daniel T. G.
    Ferreira, Vitor F.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (06) : 1080 - 1097
  • [27] MECHANISM OF P-QUINONE METHIDE INITIATED CYCLIZATION REACTIONS TERMINATED BY ALKENES - 1,2-HYDROGEN VS 1,3-HYDROGEN MIGRATION
    ANGLE, SR
    HOSSAIN, MA
    TETRAHEDRON LETTERS, 1994, 35 (26) : 4519 - 4522
  • [28] The synthesis of some chromans via o-quinone-methide intermediates
    Büyükkidan, B
    Bilgiç, S
    Bilgiç, O
    SYNTHETIC COMMUNICATIONS, 2001, 31 (08) : 1263 - 1270
  • [29] MECHANISM OF P-QUINONE METHIDE INITIATED CYCLIZATION REACTIONS TERMINATED BY ALKENES - 1,2-HYDROGEN VS 1,3-HYDROGEN MIGRATION
    ANGLE, SR
    HOSSAIN, MA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 102 - ORGN
  • [30] REDUCTION OF DAUNOMYCIN IN DIMETHYL-SULFOXIDE - LONG-LIVED SEMIQUINONES AND QUINONE METHIDE AND FORMATION OF AN ENOLATE AT THE 14-POSITION VIA THE QUINONE METHIDE
    GAUDIANO, G
    FRIGERIO, M
    BRAVO, P
    KOCH, TH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) : 3107 - 3113